Ticlopidine → HCID 12570081, compound

HRID 2299272Notes

Reaction equation

HRID 2299272 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([Cl:17])=[C:5]([CH2:7][N:8]2C[C:12]3[CH:13]=[CH:14][S:15][C:11]=3[CH2:10][CH2:9]2)[CH:6]=1.S1C=CC=C1C1[O:25]C1.ClC1C=CC=CC=1CN>>[S:15]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH:10]([OH:25])[CH2:9][NH:8][CH2:7][C:5]1[CH:6]=[CH:1][CH:2]=[CH:3][C:4]=1[Cl:17]

Participants

4

Reactant 3

HCID 5472TiclopidineHCID 666482-ChlorobenzylamineHCID 10866336Thiophene, 2-oxiranyl-

Product 1

HCID 12570081HCID 12570081, compound

Procedure

Literature precedent for ticlopidine (J. P. Maffrand, R. Boigegrain, Heterocycles, 1979, 12, 1479; FR 2,424,278) shows that (2-thienyl)ethylene oxide 14 reacts with o-chlorobenzylamine to provide the desired N-(2-(2-thienyl)-2-hydroxyethyl)-o-chlorobenzylamine in low yield due to lack of regioselectivity in the epoxide ring opening (Scheme 5).

Sources & evidence

ORD record
ord-5430097adf0d4b4f94f3ebcac760c750
Source dataset
uspto-grants-2002_12
Patent number
US06495691B1

Reaction notes

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